You can run SBS side-by-side for 21 days on the same subnet.
If you DCPromo the old SBS to remove ADDS then that limit goes down to 7. If that seven days was long gone then the old SBS would start rebooting

You can build the new server with the same servername, IP, subnet and domain as long as you keep it isolated from the current production domain. All user accounts will have to be recreated on the SBS2011 box. The email and files will have to be manually moved to the SBS2011 box. Don't think you can do a forklift of the Exchange databases but research this to confirm. All workstations will have to be removed from the SBS2k8 domain and joined to the SBS2011 domain (hopefully not alot of workstations). You will probably want to migrate everything from the SBS2k8 box to a USB hard drive then shut it down and bring the SBS2011 box into production.

Personally I prefer the swing migration method http://www.sbsmigration.com/ but I completely understand your current situation. I've done what you are proposing to create a new clean server.

You could install the new SBS instance in Migration Mode and try to pull both AD and Exchange across using that method.

Swing would give you the opportunity to clean up AD and GPO structures before deploying the newly minted SBS 2011 STD into production.

Depending on what you mean by the need to clean things up, either method can work well. We run migrations regularly here (keep guides on our blog) using the Microsoft method with Swing being our fallback for situations where clean up is required.

You will need to keep the new SBS 2011 VM isolated from the production network how ever you decide to do that. I would recommend bringing another VMware box online if possible then move it to your production esxi box. Not sure you can isolate it on the same VMware box but I'm no expert on VMware. I would have to test it on a box here but don't have time in the next few days to get to it. Sorry.

Manage projects of all sizes how you want. Great for personal to-do lists, project milestones, team priorities and launch plans.
- Combine task lists, docs, spreadsheets, and chat in one
- View and edit from mobile/offline
- Cut down on emails

You can run SBS side-by-side for 21 days on the same subnet.
If you DCPromo the old SBS to remove ADDS then that limit goes down to 7. If that seven days was long gone then the old SBS would start rebooting itself or shutting down.

SBS MythBusted. SBS can run side-by side.

DHCP can only run on one server.
DNS and DHCP would be set up on the new server.
Domain name should be different in some way so as to avoid Group Policy Tattooing.

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